Month: January 2021

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3339-73-9 as follows. Product Details of 3339-73-9

General procedure: An aqueous solution of metal (Li/Na) carbonate (4.5mmol in 50ml) was added drop wise to a well-stirred solution of NPA (9.1mmol) in ethanol (40ml) at room temperature separately. The pH (6-7) adjusted solution was stirred with heating (60C) for next 4h and then set aside for crystallization. After four weeks, 0.48g (48% yield) for each 1b and 2b of colourless single crystals were obtained.

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nadeem, Muhammad; Bhatti, Moazzam H.; Yunus, Uzma; Mehmood, Mazhar; Asif, Hafiz Muhammad; Mehboob, Shoaib; Floerke, Ulrich; Inorganica Chimica Acta; vol. 479; (2018); p. 179 – 188;,
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Related Products of 59-48-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Nitro-2-oxindole 2-Oxindole (6.5 g) was dissolved in 25 ML concentrated sulfuric acid and the mixture maintained at -10 to -15 C. while 2.1 ML of fuming nitric acid was added dropwise.. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hr and poured into ice-water.. The precipitate was collected by filtration, washed with water and crystallized from 50% acetic acid.. The crystalline product was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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These common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: indolines-derivatives

5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 53f (30 mg, 0.09 mmol) and 4-methyl-1,3-dihydro-indol-2-one (12 mg, 0.08 mmol) were dissolved in 156mul of ethanol, and added with 4.4mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45C for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml¡Á2) and dried to obtain the title compound (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one76(12 mg, yield 30%) as a orange solid. MS m/z (ESI): 465.2(M+1) 1NMR(400 MHz, DMSO-d6) delta13.71(s, 1H, pyrrole-NH),10.92 (s, 1H, indole-NH), 7.57(s, 1H, -CH=C), 7.07?6.77(m, 3H, -ArH) , 4.72(d, 1H, -OH),3.90(m, 1H, -CHOH), 3.78(dd, 1H, seven membered ring outer amide-NCH2), 3.58(t, 4H, morpholin intra 2¡Á-CH2O), 3.40(m, 2H, seven membered ring -NCH2), 3.17(dd, 1H, seven membered ring outer amide-NCH2), 2.94(t, 2H, pyrrole-CH2), 2.59(s, 3H, benzylmethyl), 2.44(m, 4H, morpholin intra 2¡ÁCH2N), 2.39(s, 3H, pyrrole -CH3), 2.29(m, 2H, morpholin outer-NCH2), 2.08(m, 2H, seven membered ring CH2-CH2-CH2).

The synthetic route of 4-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
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Reference of 19155-24-9, These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 3,3-dimethyloxindole 41 (100 mg,0.62 mmol, 1.00 equiv) and Cs2CO3 (403 mg, 1.24 mmol, 2.00 equiv) in THF (3.10mL) was added m-nitrobenzyl bromide (335 mg, 1.55 mmol, 2.50 equiv). Thereaction mixture was stirred overnight. Then, the reaction mixture was extracted withEtOAc (3 x 4 mL) and washed with brine. The combined organic phases were driedover MgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?3-nitrobenzyl-3,3-dimethyloxindole 3b (170 mg, 92percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.16 ? 8.11 (m, 2H),7.60 (ddt, J = 7.7, 1.8, 0.9 Hz, 1H), 7.53 ? 7.48 (m, 1H), 7.26 ? 7.24 (m, 1H), 7.17 (td,J = 7.7, 1.3 Hz, 1H), 7.07 (td, J = 7.5, 1.0 Hz, 1H), 5.01 (s, 2H), 1.46 (s, 6H); 13CNMR (126 MHz, CDCl3) delta 181.7, 148.6, 141.1, 138.5, 135.9, 133.3, 130.1, 127.9,123.2, 122.9, 122.8, 122.2, 108.7, 77.2, 44.4, 43.0, 24.7; IR (Neat Film NaCl) 2969,1652, 1538, 1348, 1011, 933, 761; HRMS (MM: ESI-APCI+) m/z calc?d forC17H17N2O3 [M+H]+ : 297.1234; found: 297.1241.

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3335-98-6, name is 1-Phenyloxindole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Phenyloxindole

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 446292-08-6 as follows. Computed Properties of C22H19N3O6

10 g (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phe- nyl)oxazolidin-5-yl)methyl)isoindoline- i ,3-dione of Formula (I), 70 ml methanol and 60 ml monomethyl amine were added to REF at 25 C. to 35 C. The reaction was heated to 60 C. to 65 C. for i-2 hours. To the reaction mass L (+)- mandelic acid (3.6 g) was added and maintained for 30 minutes. The reaction mass was cooled to 45 to 50 C. and maintained for 30 minutes. The reaction mass was cooled to 25 to 35 C. and maintained for 30 minutes. The product was filtered and washed with methanol (50 mlx2) afforded the L(+)-mandelate salt of(S)-4-(4-(5-(aminomethyl)-2-oxo-ox- azolidin-3-yl)phenyl)morpholin-3-one of Formula (JM).

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CADILA HEALTHCARE LIMITED; Dwivedi, Shriprakash Dhar; Prasad, Ashok; Pal, Daya Ram; Sharma, Mukul Hari Prasad; Jain, Kuldeep Natwarlal; Patel, Naitik Bharatbhai; US2014/378682; (2014); A1;,
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552330-86-6, name is 5-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 552330-86-6

Step 1: tert-Butyl 5-bromo-1-oxoisoindoline-2-carboxylate (0650) (0651) (Boc)2O (69.5 g, 318.33 mmol) was added slowly to 5-bromoisoindolin-1-one (45 g, 212.22 mmol) and DMAP (38.9 g, 318.33 mmol) in acetonitrile (1000 mL) at room temperature over a period of 30 minutes under nitrogen. The resulting solution was stirred at this temperature for 12 hours. The solvent was removed under reduced pressure. The residue was treated with water (500 mL), extracted with DCM (3¡Á500 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford brown oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford tert-butyl 5-bromo-1-oxoisoindoline-2-carboxylate (55.0 g, 83%). (0652) LC/MS: m/z=256,258 [M-tBu+H]+. 1H NMR (400 MHz, CDCl3) delta 1.62 (s, 9H), 4.76 (s, 2H), 7.63-7.66 (m, 2H), 7.78 (d, J=8.0 Hz, 1H).

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Application of 65826-95-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 7; 1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indol-6-ylamineThe synthetic procedure used in this preparation is outlined in Scheme G. Step 1 5-Methyl-6-nitroindolineTo a solution of 2.5 g 5-methylindoline in 20 ml. of concentrated. Sulfuric acid at 0 C. was added in portions 1.7 g of potassium nitrate, keeping the temperature below 5 C. After the addition was complete, the mixture was stirred at 5 C. for ten minutes and then poured onto ice. The aqueous solution was made alkykline with 10% sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine and then dried over sodium sulfate, filtered and concentrated in vacuo. The residue crystallized on standing to give 2.75 g of 5-methyl-6-nitroindoline as a yellow solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Methylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berger, Jacob; Caroon, Joan Marie; Krauss, Nancy Elisabeth; Walker, Keith Adrian Murray; Zhao, Shu-Hai; Lopez-Tapia, Francisco Javier; US2010/160373; (2010); A1;,
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Electric Literature of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a 4-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester A mixture of 4-hydroxy-benzoic acid methyl ester (3.01 g, 19.8 mmol), 2-(5-bromo-pentyl)-isoindole-1,3-dione (3.9 g, 13.2 mmol), and K2CO3 (1.82 g, 13.2 mmol) in acetone (150 mL) was heated to reflux for 24 hrs. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude was diluted in EtOAc and washed with 1N NaOH and brine. The organic layer was dried over sodium sulfate. The solvents were removed in vacuo. The crude was recrystallized from EtOAc to afford the title compound as a white solid (4 g, 83%). 1H-NMR (CDCl3): delta 7.95-7.98 (m, 2H), 7.83-7.86 (m, 2H), 7.70-7.73 (m, 2H), 6.86-6.89 (m, 2H), 4.00 (t, 2H, J=6.22 Hz), 3.88 (s, 3H), 3.73 (t, 2H, J=7.29 Hz), 1.82-1.89 (m, 2H), 1.73-1.81 (m, 2H), 1.50-1.57 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(5-Bromopentyl)phthalimide, its application will become more common.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2004/9995; (2004); A1;,
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Electric Literature of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 50 1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(1,3-dioxoisoindolin-5-yl)piperidine-3-carboxamide Procedure: To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (50 mg, 0.12 mmol) and 5-aminoisoindoline-1,3-dione (19 mg, 0.12 mmol) in pyridine (8 mL) was added POCl3 (0.3 mL, 3.23 mmol) at 0 C., the reaction mixture was stirred at room temperature for 4 hours, a sat.NaHCO3 solution was added slowly, the solvent was removed in vacuo, water (5 mL) and methanol (2 mL) were added. The precipitate was collected by filtration and washed with water (5 mL) and methanol (5 mL) to afford 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(1,3-dioxoisoindolin-5-yl)piperidine-3-carboxamide (27 mg, 40.0%) as an orange solid. 1H NMR (300 MHz, DMSO): delta 11.20 (s, 1H), 10.59 (s, 1H), 9.64 (s, 1H), 8.83 (s, 1H), 8.13 (s, 1H), 7.86-7.73 (m, 2H), 7.63 (s, 1H), 7.38-7.29 (m, 1H), 6.78 (s, 1H), 4.77 (d, 1H, J=12.0 Hz), 4.62 (d, 1H, J=12.3 Hz), 3.66 (s, 3H), 3.61 (s, 3H), 3.16-2.94 (m, 2H), 2.60-2.55 (m, 1H), 2.04-2.01 (m, 1H), 1.76-1.72 (m, 2H), 1.52-1.41 (m, 1H). LC-MS: 560 [M+H]+, tR=1.49 min. HPLC: 99.49% at 214 nm, 99.47% at 254 nm, tR=5.33 min.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
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